SYNTHESIS OF UREIDE DERIVATIVES OF 2-AMINO-3-CARBETOXY(CYANO) THIOPHENES AND STUDY OF THEIR CYCLIZATION
DOI:
https://doi.org/10.32782/pcsd-2024-1-3Keywords:
thieno[2,3-d]pyrimidines, ureide derivatives of 2-amino-3-carbetoxy(cyano)thiophenes, synthesis, cyclizationAbstract
This work is devoted to the study of the synthesis of ureide derivatives of 2-amino-3-carbetoxy(thio)thiophenes and their cyclization to create new effective drugs based on them, which is one of the most urgent tasks of organic chemistry and pharmaceutical science. The aim of this work was to synthesize ureide derivatives of 2-amino-3-carbetoxy(cyano) thiophenes and study their cyclization. Methodology. For the synthesis of the initial ureides, we studied the interaction of 2-amino-3-carbetoxy(cyano)thiophenes with phenylisocyanate, isolated the initial thiophenes (2.1a-d) from the reaction medium, and developed a method for the synthesis of ureide derivatives (3.1a-c) containing an ester group at position 3, which involves the use of a nonpolar solvent, benzene, with an optimal synthesis time of approximately 3 hours. The obtained compounds were characterized by spectroscopic methods, including UV, IR and 1H NMR spectroscopy. It was found that the reaction can be carried out by boiling in benzene, which requires an increase in the synthesis time; individual ureides (3.1e,f) were obtained in 75% yield when boiled for 3.5 hours. It was found that the formation of ureide derivatives did not occur under the conditions of the synthesis of similar thioureides described in the literature. An alternative method for the synthesis of ureide derivatives containing an ester group at position 3, which involves the use of a nonpolar solvent, benzene, has been proposed. The optimum conditions for the synthesis of ureide derivatives with a cyanogen group in position 3 were found, namely, heating 2-amino-3-cyanothiophenes with phenylisocyanate for 3 hours in the medium of toluene or a mixture of xylene isomers. Conclusions. Methods for the synthesis of ureide derivatives of 2-amino-3-carbetoxy(thio)thiophenes, sodium salts of 2-oxy-4-oxo(imino)-3-phenyl- 5-R-6-R`-thieno[2,3-d]pyrimidines, 2,4-dioxo- and 2-oxo-4-imino-3-phenyl-5-R-6-R`-thieno[2,3-d]pyrimidines were developed and their cyclization was studied.
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